The music history of colonial Korea and Taiwan has thus far been researched separately. This separation can also be observed in many other fields. Considering the historical, cultural, and linguistic differences between the two regions, it is understandable that each has developed its own body of scholarship. Moreover, historical consciousness rooted in nationalist and nativist perspectives has further motivated and shaped such research trajectories. However, when we examine these two histories side by side, we find not only their respective particularities but also numerous aspects that were intertwined. Furthermore, contemporary trends in Japan proper, and even broader global currents, were deeply entangled in these developments. This presentation introduces a theoretical approach to these entanglements through the concept of “cross-colonial counterpoint,” taking as an example the contemporaneous development of the record industries and popular songs in colonial Korea and Taiwan. Specifically, I divide the timeline into four corresponding periods and examine cases from Korea and Taiwan in parallel, following a chronological structure. The analysis focuses on three key aspects: record labels, recorded genres, and the intermediary processes that connect the two. By proposing a periodization that reveals both shared and divergent developments, this presentation seeks to illuminate aspects of cross-colonial counterpoint while also attending to historical trajectories unique to Korea and Taiwan. This perspective has several aims. In terms of historical narrative, it seeks to relativize the conventional discourse of “influence” from Japan proper and other imperial centers. It also calls for a reconsideration of static “comparative” frameworks between Korea and Taiwan. Rather than relying on colonialist notions of historical “time lag” or essentialist comparisons, this approach foregrounds the regional and global contemporaneity of these developments, and brings into focus the transimperial interrelations and power structures that shaped them.